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Issue 12, 2014
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Solvent-induced conformational changes in cyclic peptides: a vibrational circular dichroism study

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Abstract

The three-dimensional structure of a peptide is strongly influenced by its solvent environment. In the present study, we study three cyclic tetrapeptides which serve as model peptides for β-turns. They are of the general structure cyclo(Boc-Cys-Pro-X-Cys-OMe) with the amino acid X being either glycine (1), or L- or D-leucine (L- or D-2). Using vibrational circular dichroism (VCD) spectroscopy, we confirm previous NMR results which showed that D-2 adopts predominantly a βII turn structure in apolar and polar solvents. Our results for L-2 indicate a preference for a βI structure over βII. With increasing solvent polarity, the preference for 1 is shifted from βII towards βI. This conformational change goes along with the breaking of an intramolecular hydrogen bond which stabilizes the βII conformation. Instead, a hydrogen bond with a solvent molecule can stabilize the βI turn conformation.

Graphical abstract: Solvent-induced conformational changes in cyclic peptides: a vibrational circular dichroism study

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Supplementary files

Article information


Submitted
28 Nov 2013
Accepted
27 Jan 2014
First published
11 Feb 2014

This article is Open Access

Phys. Chem. Chem. Phys., 2014,16, 5627-5633
Article type
Paper

Solvent-induced conformational changes in cyclic peptides: a vibrational circular dichroism study

C. Merten, F. Li, K. Bravo-Rodriguez, E. Sanchez-Garcia, Y. Xu and W. Sander, Phys. Chem. Chem. Phys., 2014, 16, 5627
DOI: 10.1039/C3CP55018D

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